Begin by making the caramel as this is needed for the creme caramel and the pineapple.
Place 1 cup of sugar in a heavy saucepan over high heat and cook until a bronze color. Swirl the pan as it begins to color to mix the sugar and caramel. Once the caramel has reached its color, very carefully pour a little of the caramel, just enough to cover the bottom, into 6 (2-ounce) timbales or ramekins.
Using the remaining caramel, add the orange juice, rum, and vanilla extract to the pan. Return to the stove to dissolve the caramel. When all is melted, pour the caramel mixture over the pineapple slices and combine all of the ingredients for the pineapple marinade. Allow the mixture to cool for approximately 3 to 4 hours and refrigerate.
To make the creme caramel, combine the warm milk and vanilla. In a separate bowl, combine the egg yolks, eggs, and remaining 3 tablespoons of sugar and beat well.
Mix the warm milk and the egg mixture well to make a thin custard.
Pour the custard into the ramekins, place in a deep tray, fill with 1 inch of hot water, and place in the oven for approximately 20 to 25 minutes until set.
Remove from oven and allow to cool completely.
To serve, use a small knife and score the outside rim of the ramekins to help release the creme caramels. Turn creme caramels onto a plate, add a few slices of caramelized pineapple and raisins, drizzle a little of the juice around the plate, and finish with a scoop of banana ice cream.
